Hydrochloric Acid → HCID 69287051, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of bis(6-bromobenzofuran-2-yl)methanone (84) (3.50 g, 8.62 mmol) and CuCN (6.12 g, 69.0 mmol) was heated under reflux in dry quinoline (10 mL) for 2 hours. The hot reaction mixture was poured into 2 M HCl solution and resulting mixture was stirred at 50-70° C. for 1 hour. Olive precipitate was filtered off, dried under high vacuum and suspended into 300 mL chlorobenzene. The mixture was stirred for 1 hour at room temperature, insoluble material was separated, and filtrate was concentrated. A dark solid residue (2 g, 78%) was purified by column chromatography (SiO2, CHCl3) to afford desired product as light yellow crystals (1.62 g, 63%): mp 173-174° C. (CHCl3). 1H NMR (DMSO-d6) δ7.96 (d, J=8.2 Hz, 2H), 7.77 (d, J=7.7 Hz, 2H), 7.46 (tt, J=8.2, 7.7 Hz, 2H), 7.09 (s, 2H), 4.64 (s, 2H). HPLC (method B) tR 7.92 min (100.00 area %). Anal. (C19H10N2O2) C, H, N.

Provenance & Evidence